3-Iodo-6-methoxy-2-methylbenzo[b]thiophene → 6-Methoxy-2-methylbenzo[b]thiophene

HRID 1192019Notes

Reaction equation

HRID 1192019 reaction equation
[Li]C(C)(C)C.I[C:7]1[C:8]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:9]=2[S:10][C:11]=1[CH3:12]>C1COCC1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:8]2[CH:7]=[C:11]([CH3:12])[S:10][C:9]=2[CH:13]=1

Participants

4

Reactant 2

HCID 672872223-Iodo-6-methoxy-2-methylbenzo[b]thiopheneHCID 178418306HCID 178418306, compound

Product 1

HCID 221434866-Methoxy-2-methylbenzo[b]thiopheneYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

t-BuLi (1.7 M in pentane; 0.32 ml; 0.54 mmol) was added to a solution of the 3-iodo-6-methoxy-2-methylbenzo[b]thiophene (0.0863 g; 0.27 mmol) in anhydrous THF (2.5 ml) at −78° C. under N2. The mixture was allowed to warm up to 0° C. and quenched by the addition of saturated NH4Cl (1 ml). This was diluted to 15 ml with diethyl ether and washed with 5% NaHCO3 (10 ml), dried over anhydrous MgSO4, filtered off and filtrate evaporated to dryness. The residue was purified by flash column chromatography (SiO2, hexane, hexane/ethyl acetate 9.5:0.5) to give the title compound (0.024 g; 50% yield) as colourless solid. 1H-NMR (CDCl3) 2.53 (s, 3H); 3.84 (s, 3H); 6.86 (s, 1H); 6.92 (dd, 1H, J=2.24, 8.87 Hz); 7.222 (d, 1H, J=2.24 Hz); 7.51 (d, 1H, J=8.67 Hz).

Workup

  1. customquenched by the addition of saturated NH4Cl (1 ml)
  2. additionThis was diluted to 15 ml with diethyl ether
  3. washwashed with 5% NaHCO3 (10 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered off
  6. customfiltrate evaporated to dryness
  7. customThe residue was purified by flash column chromatography (SiO2, hexane, hexane/ethyl acetate 9.5:0.5)

Sources & evidence

ORD record
ord-694c169a2db64d31b6009b12ef31acc1
Source dataset
uspto-grants-2014_03
Patent number
US08680135B2

Reaction notes

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